Painter Hall, the oldest extant college building in Vermont, was the result of the "contest" of 1810, although actual construction dates from 1814 – 1816. Originally called "West College" (as opposed to the Academy Building, or "East College"), this building is as practical and straightforward as the town and the men who furnished the $8000 for its construction. The college needed space, space for any of a variety of purposes; and since the largest, most multi-purpose structures with which the townspeople had experience were mill buildings, it is essentially a mill building that they constructed for the college. Not that this was felt to be a shortcoming in any way. The new hall was a focus for local pride. Under the supervision of trustee Rufus Wainwright, the structure was built with local (Weybridge) stone by local masons. It had multiple entries (originally without porches) and staircases giving access to thirty-six rooms with fireplaces. The regular rows of windows and multiple great chimneys give it much the appearance of structures built to house mill-workers in Massachusetts and New Hampshire. The flexibility of the building has paid off over the years. In time a library with reading room and multi-level stacks occupied part of the north end, a two-story gymnasium filled the upper floors of the south end. In 1898 Painter contained a reading room, the only lavatories on campus, a classroom, a library, and six student rooms. Today it is wholly a dormitory.
Shortly after its completion, the new building was responsible for the loss of a popular faculty member. In the fall of 1817 twenty-eight-year-old professor of Greek and Latin, Solomon M. Allen, climbed up on the roof to fix a defective chimney. Before the eyes of horrified onlookers, the scaffolding gave way. Allen slid down the roof and died when he fell to the ground.
In 1905 Kappa Delta Rho, national social fraternity, was founded in Painter Hall, a fact that is commemorated by the plaque at the south end of the building.